Roger Ibbotson: Why Isn’t Everyone Rich When the Math Is This Simple? | #651

Today’s guest is Roger Ibbotson, a finance professor at Yale for four decades and founder of Ibbotson Associates. In today’s episode, Roger shares a century of stock and bond data and how one dollar became fifteen thousand in large caps over a hundred years. He explains why most people never capture those returns, and why total returns went unmeasured for decades. To close, Roger makes the case for young investors owning nothing but stocks and forecasts the next twenty five years.

FT’s Robin Wigglesworth: Why Bonds, Not Stocks, Rule Everything Around Us | #650

Today’s guest is Robin Wigglesworth, editor of FT Alphaville at the Financial Times and the author of A Fabulous Debt: The Epic Story of How Bonds Built the Modern World. In today’s episode, Robin makes the case that bonds, not stocks, are the bedrock of finance and quietly built the modern world. He explores the hidden plumbing beneath it, from the $12 trillion repo market to the leverage lurking in Treasuries, and why fixed income ETFs are rewiring how bonds trade.

Why Gold Stopped Being a Commodity (AllianceBernstein’s Inigo Fraser Jenkins) | #649

Today’s guest is Inigo Fraser Jenkins, Chief Investment Strategist at AllianceBernstein. In today’s episode, Inigo argues that the golden era of easy diversification and high real returns is ending. He defends US equity exceptionalism while declining to defend the dollar. To close, he makes the case for gold and explains why bonds may no longer diversify equities.

Paul Kedrosky: AI is the First Bubble With Every Ingredient at Once | #648

Today’s guest is Paul Kedrosky, a fellow at the MIT Institute for the Digital Economy, partner at SK Ventures and former sell-side analyst. In today’s episode, Paul Kedrosky explains why AI sits at the intersection of every force behind the biggest bubbles. He walks through why tokens are the fastest-deflating commodity ever, why more than half the data center buildout runs on debt instead of cash flow, and why an IPO wave pressures the market’s biggest winners. To close, Paul argues AI already drives most US GDP growth, and revisits how badly humans misjudge scale.

Jerry Parker on Big Game Hunting in the Market | #647

Today’s guest is Jerry Parker, founder and CEO of Chesapeake Capital and one of the original Turtles trained by Richard Dennis. Together we run the Cambria Chesapeake Pure Trend ETF (MFUT). In today's episode, Jerry explains why managed futures isn't the same as trend following. He breaks down the math and psychology of hunting outliers, letting a few winners pay for many small losses, and why he'd never chase crisis alpha at the cost of returns. To close, Jerry explains why MFUT trades individual stocks rather than just indices.

David Booth: 45 Years to $1 Trillion at Dimensional | #646

Today’s guest is David Booth, founder of Dimensional Fund Advisors, which now manages over $1 trillion. He studied under Eugene Fama at Chicago and helped build one of the first index funds at Wells Fargo. In today’s episode, David traces Dimensional’s arc from indexing’s earliest days at Wells Fargo to crossing $1 trillion in AUM this year. He shares what Gene Fama said when he got the call, the story of driving a client to Chicago to walk through the Fama-French paper, and why AI investing looks like the California gold rush. To close, David makes the case for judging yourself by decisions, not outcomes.

Luke Gromen: The Bull Market That Loses You Money | #645

Welcome back, everyone. Today we have an awesome episode. Today’s guest is Luke Gromen, founder of the macro research firm Forest for the Trees, or FFTT. In today's episode, Luke Gromen argues that free trade is dead, and the US is pivoting to Hamiltonian economics: tariffs, reshoring, and a neutral reserve asset. He explains why the US Treasury can no longer be the world's reserve asset, why long bonds have become certificates of confiscation, and why gold belongs in every portfolio. To close, Luke explains why AI has become a snake eating its own tail on the government's tax base.

Teaser: Investing in America: The Rise Of A 250-Year Bull Market | #644

In today's episode, I read the opening of my new book, Investing in America: The Rise of a 250-Year Bull Market, plus a couple of sidebars. The book is available now. Grab a copy on Amazon or learn more at www.investinginamericabook.com.

Liaquat Ahamed on the Railroad Bubble That Crashed the World | #642

Today’s guest is Liaquat Ahamed, the Pulitzer Prize–winning author of Lords of Finance: The Bankers Who Broke the World, one of the greatest financial history books ever written. His new book is called 1873: The Rothschilds, the First Great Depression, and the Making of the Modern World. In today’s episode, Liaquat shares the story of the world’s first truly global financial crisis. He walks through the Rothschild-led bond boom that funded railroads on three continents, the German IPO mania sparked by French war reparations, and the monetary blunder of abandoning silver that turned a crash into twenty years of deflation.

Zombie Stocks and Hidden Value With Bob Robotti | #641

Today’s guest is Bob Robotti, founder and CIO of Robotti and Company Advisors, which he’s been running the firm since 1983. In today’s episode, Bob explains why volatile markets driven by passive flows keep handing opportunities to stock pickers. He makes the case for offshore oil services and homebuilders, shows why zombie companies can be dollars trading for 20 cents, and argues 2% inflation is a pipe dream. To close, Bob shares the biggest loss of his career, selling a winner too early.

Muddy Waters’ Carson Block on How AI Could Unwind the S&P 500 | #640

My guest today is Carson Block, founder of Muddy Waters Research & Muddy Waters Capital and one of the last short sellers still standing. In today’s episode, Carson Block explains why he thinks AI could displace 15% of knowledge workers and unwind the market’s biggest stocks. He breaks down his short of SoFi’s aggressive loan accounting, why record-tight credit spreads worry him, and how he trades that risk with put spreads. To close, Carson explains why he still calls China uninvestable and recounts his hardest battles.

Joseph Moore: How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn’t) | #639

My guest today is Joseph Moore, a historian and former professor who spent over a decade in the archives studying 300 years of American financial advice, which he explains in his new book, How to Get Rich in American History: 300 Years of Financial Advice That Worked (& Didn’t). In today’s episode, Joseph explains what 300 years of American financial advice reveals about getting rich. He shares why real estate barely appreciated for a century, why bonds beat stocks for decades, and how modern investing advice was born chasing inflation and taxes. To close, Joseph reveals the five timeless principles that built wealth in every era.

The Secret Sauce Behind 250 Years of American Success (McKinsey’s Rebecca Anderson) | #638

Today’s guest is Rebecca Anderson, a Senior Fellow at the McKinsey Global Institute, McKinsey’s business and economics research arm. She leads research on economic growth and the financial system, in the United States and globally. In today’s episode, Rebecca shares her McKinsey report on what has powered America’s economy for 250 years: natural endowments, a culture of entrepreneurship, and the institutions that harnessed them. She examines labor force dynamism in the age of AI, the $2 trillion cost of reindustrialization, and a global balance sheet stretched to record highs.

Ben Carlson: The Numbers That Break Your Brain About Long Term Investing | #637

Today’s guest is Ben Carlson of Ritholtz Wealth Management, author of A Wealth of Common Sense and host of the Animal Spirits podcast. In today’s episode, Ben unpacks the counterintuitive math behind long term investing. He reveals that picking the wrong asset every year still makes money, that the average up year tops 20%, and that stocks grow less volatile than bonds the longer you hold. To close, Ben explains why patience has never been harder.

Meb Faber's Investing in America, Out July 4th (Investing in America Series) | #636

In today's special episode, Meb celebrates the release of his new book, Investing in America, a coffee table history of the 250 year bull market. He explains the magic of compounding, why every decade feels like chaos, and the surprising fact that stocks become less volatile than bonds over long horizons. To close, Meb weighs today's valuations against the long view.

Bryan Taylor: There Is No Equity Risk Premium (Investing in America Series) | #635

Today’s guest is Bryan Taylor, founder and chief economist of Finaeon, which has the most comprehensive database of historical financial market data in the world. He's just published Five Financial Eras: How Financial Markets Transformed the World. In today’s episode, Bryan explains his TWIG framework of trade, war, inflation, and government, and how their combination drives returns across centuries of market history. He challenges the belief in a fixed equity risk premium and revisits seven decades of negative real bond returns. To close, Bryan explains why the post-1981 playbook no longer applies.

Jim Grant: AI Is “One of the Greatest Bubbles of All Time” (Investing in America Series)| #634

Today’s guest is Jim Grant, founder and editor of Grant’s Interest Rate Observer, which he’s been publishing since 1983. He’s a financial historian and one of the most well-respected Observers on Wall Street. In today’s episode, Jim Grant explains why AI may be one of the greatest bubbles of all time, alongside the railroads and the dot-com era. He reframes deflation as progress, questions how murky the $2 trillion private credit market is, and explains why the Fed can’t aggressively fight inflation. To close, Jim makes his case for gold and revisits 1984, which he calls the clearest example of how strange markets can be.

Charley Ellis on How America Actually Got Built (Investing in America Series) | #633

My guest today is Charles Ellis, founder of Greenwich Associates, longtime member of Yale’s investment committee, and author of more than 20 books, including the classic Winning the Loser’s Game. In today’s episode, Charley reflects on writing the first major book on share repurchases 50 years ago, when the idea was so foreign that Goldman mailed it to 1,000 corporations as a “legitimizer.” Charley also walks us through his new book, Great American Investments: A History of the Bold Initiatives that Shaped a Nation, covering 14 audacious public investments from the Louisiana Purchase to the Marshall Plan. He explains how each came down to one or two obsessed individuals, why Alaska turned out to be the bargain of the century, and how Frances Perkins muscled Social Security into law. As the episode winds down, he shares the lunch with Sandy Gottesman in the early 1970s that led him to buy Berkshire Hathaway at $700 a share — and hold it ever since.

William Goetzmann: From Babylon to Bubbles — A 5,000-Year History of Finance (Investing in America Series) | #632

Today’s guest is Will Goetzmann, Professor of Finance at the Yale School of Management. He is an expert on financial markets and securities, investment strategies, investor behavior and financial history. In today’s episode, Professor Goetzmann walks through 5,000 years of financial history, showing how finance shaped trade, cities, corporations, and investing. He covers the first compound interest calculation, the world’s oldest corporations and bonds, and historic bubbles from tulips to NFTs. To close, he explains why markets have repeatedly adapted through war, crisis, and uncertainty.

Meb Faber: Warren Buffett Didn't Follow His Own Advice | #631

While in Omaha for Berkshire week, Meb hopped on another podcast as a guest. It was a fun one, so we're releasing it here as well. In today's episode, Meb Faber makes the case against home country bias, pointing to Korea's near-triple and Japan's decades-long round trip as reminders that cycles always turn. He explains why shareholder yield tells a truer story than dividends, why there are now more ETFs than stocks, and why tax alpha matters more than chasing returns. To close, Meb reflects on multi-decade compounding — and the mistakes that quietly take investors out of the game.